This project is directed towards the synthesis of the naturally occurring indolequinones, mitomycin and kinamycin. These are both potently active compounds which show antibiotic and/or antineoplastic properties, and their mechanism of action may be one of bioreductive alkylation. The synthetic routes to these natural products are based upon an extensive prior study of the chemistry of azidoquinones. This class of organic azides are versatile synthetic intermediates and their chemistry will be of key importance for the current study. Three potentially general routes to the mitomycin ring system which are based upon the chemistry of azidoquinones have been discovered, and their utility and scope is under investigation. These synthetic routes all appear to be potentially general methods for the construction of indolequinones and can be used to construct a large variety of such heterocyclic quinones which may function as bioreductive alkylating agents.